Chicago, Illinois

“She said, ‘Excuse me little homie, I know you don’t know me but my name is Windy, and I like to blow trees…”

The Navy Pier Ferris Wheel is the only one I’ve ever been on that has A/C in the cars

Say hello to what I lovingly refer to as my second city — Chicago! My mom is a Chicago native, and my grandmother still lives in the area. Billy and I have a tradition of venturing out to Chicago once every year in spring or summer (we also got married here). This year, we went for Memorial Day Weekend, so the trip was short and sweet.

I will always prefer a city skyline to a country view

We stayed in a hotel near the Magnificent Mile, a prime tourist spot. We have stayed at several hotels over the years, and this last one was, unfortunately, awful. If you are thinking about booking a room with the Tremont Chicago, don’t. The rooms are musty, old, and overpriced. The only perk of staying there was that we were one block from Water Tower Place.

Instead, I recommend the following hotels:

Despite our sad accommodations, we still had an amazing time.

You can take a boat tour on the architecture of the city

With this being a quick trip and far from our first stop in Chicago, we did not do a lot of touristy things. We shopped, ate, and just walked around, enjoying the weather before the rain came through. But there are a lot of fun things we have done in Chicago over the years that I recommend to anyone.

First, if you are a STEM nerd like me, the Museum of Science and Industry should be on your list. It’s the largest science center in the Western Hemisphere and — in my sales pitch voice — it’s fun for the whole family! But really though, it is. Billy and I first went to this museum as two, childless adults and we had the best time. I even watched ducklings hatch from eggs with a small group of elementary school kids. No shame in my science game.

Young Billy in the glass box at Sears Tower

For the daredevils among us, Sears (Willis) Tower will take you to new heights *badum tuss*. This building is the second tallest skyscraper in the US, and they have an observation deck where you can see the entire city. If you are really brave, they even have clear, glass boxes that you can step into and feel as if you are floating above the city.

I’m also a big fan of history tours. I was a tour guide in Memphis for a short while, and I loved sharing fun facts about my hometown with people from all over the world. So I really enjoy sitting on the other side of the microphone and learning from someone who is just as passionate about their own city. If you have the chance, I recommend taking a crime history bus tour. There are several to choose from in the city, and I don’t think you can go wrong with any of them (pro tip: check Groupon). You learn about the Al Capone days and the St. Valentine’s Day Massacre and even about more recent crimes like the Tylenol cyanide murders in the 80s. It’s dark, sometimes gruesome, and interesting as hell.

Lake Michigan looks so inviting, and there are beaches near Navy Pier

So I’m sure at this point you have questions about two things: hot dogs and pizza. Chicago has the best of both (sorry, NYC, but I’ve had both your pizza and hot dogs, and they are disappointing). For hot dogs, you have to go to Portillo’s. I know it’s a chain, but it started in Chicago and they know what’s up. My signature order? A hot dog with everything, large cheese fries, and a large Coke. Always good.

For your deep dish pizza, you want Giordano’s. Be prepared for a 45-minute wait that your taste buds will thank you for. I’m a big fan of the Super Veggie.

Full disclosure – this was not at Giordano’s, and Giordano’s is better

Finally, for you folks looking for a little romance, I recommend taking a dinner cruise on The Odyssey Chicago. Billy and I had a great time on this cruise for our one-year anniversary. The dinner was wonderful, the DJ played great music, and the staff even gave us complimentary champagne and a special dessert. It was the perfect setting for cheesy love.

Being cute on the cruise ship

There are so many things to do in Chicago that I cannot possibly list them all in this post. Most of my recommendations center around the Magnificent Mile, but don’t be afraid to venture out to some other neighborhoods when you become more familiar with the city. Some of my favorites include Lincoln Park, Chinatown, Hyde Park, Boystown, and Loyola, and there are a lot more than that. Go visit the Windy City and see why I love it so much!

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